3-methoxyphencyclidine

Structural formula
General
Surname	3-methoxyphencyclidine
other names	3-meo-PCP; 1- [1- (3-methoxyphenyl) cyclohexyl] piperidine;
Molecular formula	C 18 H 27 NO
External identifiers / databases
PubChem	11778080
ChemSpider	9952762
Wikidata	Q223096
properties
Molar mass	273.41 g · mol -1
Physical state	firmly
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-MeO-PCP or 3-methoxyphencyclidine structurally belongs to the group of arylcyclohexylamines and is thus a derivative of ketamine and phencyclidine , which also has structural properties in common with methoxetamine and 4-MeO-PCP . It has been shown that 3-MeO-PCP acts as an NMDA receptor antagonist and SRI .

chemistry

The name 3-MeO-phencyclidine shortened 3-Me th o xy- phen yl cycl ohexyl piperidine from. Just like PCP, Ketamine, MXE, PCE etc., it comes from the group of arylcyclohexylamines. A synthesis can possibly start from 1-piperidinocyclohexanecarbonitrile (PCC), since PCC is also used as a starting material for PCP, TCP and 4-Meo-PCP. The starting material PCC is itself slightly psychoactive (0.03% of the potency of PCP), but extremely toxic.

Legal position

In Germany, 3-Meo-PCP is listed in Appendix II of the Narcotics Act (BtMG) and is therefore marketable, but not prescribable.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Ministry for Health, Social Policy and Publishing (Spain): Emerging Drugs - Clinical Committee Reports ( Memento of August 30, 2014 in the Internet Archive ), Classification, p. 22, Madrid, ISBN 978-84-920522-8-8
↑ (ACMD) Methoxetamine Report (2012) (PDF) In: UK Home Office . P. 14, October 18, 2012. Accessed November 12, 2015.
↑ Bryan L. Roth, Simon Gibbons, Warunya Arunotayanun, Xi-Ping Huang, Vincent Setola, Ric Treble, Les Iversen, Kenji Hashimoto: The Ketamine Analogue Methoxetamine and 3- and 4-Methoxy Analogues of Phencyclidine Are High Affinity and Selective Ligands for the Glutamate NMDA Receptor. In: PLoS ONE . 8, 2013, p. E59334, doi : 10.1371 / journal.pone.0059334 .
↑ Vignon J, Vincent JP, Bidard JN, Kamenka JM, Geneste P, Monier S, Lazdunski M: Biochemical properties of the brain phencyclidine receptor . In: European Journal of Pharmacology . 81, No. 4, July 1982, pp. 531-42. doi : 10.1016 / 0014-2999 (82) 90342-9 . PMID 6214413 .
↑ Manallack DT, Wong MG, Costa M, Andrews PR, Beart PM: Receptor site topographies for phencyclidine-like and sigma drugs: predictions from quantitative conformational, electrostatic potential, and radioreceptor analyzes . In: Molecular Pharmacology . 34, No. 6, December 1988, pp. 863-79. PMID 2849051 .
↑ Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R: Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs . In: Pharmacology, Biochemistry and Behavior . 32, No. 3, March 1989, pp. 699-705. doi : 10.1016 / 0091-3057 (89) 90020-8 . PMID 2544905 .
↑ Manallack DT, Davies JW, Beart PM, Saunders MR, Livingstone DJ: Analysis of the biological and molecular properties of phencyclidine-like compounds by chemometrics . In: drug research . 43, No. 10, October 1993, pp. 1029-32. PMID 8267664 .
↑ Synthesis of 4-Methoxy-PCP
^ The detection of PCC contamination in PCP and TCP
↑ Illicit Synthesis of Phencyclidine (PCP) and Several of Its Analogs
↑ Andreas Kelich: Encyclopedia of Drugs - PCC
↑ 44th meeting of the Committee of Experts in accordance with Section 1 (2) of the Narcotics Act (BtMG) on May 4th, 2015 at 1 p.m. at the Federal Institute for Drugs and Medical Devices (BfArM, Bonn) . Federal Institute for Drugs and Medical Devices (BfArM). April 4, 2015. Archived from the original on August 28, 2017. Retrieved July 1, 2015.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] Ministry for Health, Social Policy and Publishing (Spain): Emerging Drugs - Clinical Committee Reports ( Memento of August 30, 2014 in the Internet Archive ), Classification, p. 22, Madrid, ISBN 978-84-920522-8-8

[ACMD_MXE_report-3] (ACMD) Methoxetamine Report (2012) (PDF) In: UK Home Office . P. 14, October 18, 2012. Accessed November 12, 2015.

[DOI10.1371/journal.pone.0059334-4] Bryan L. Roth, Simon Gibbons, Warunya Arunotayanun, Xi-Ping Huang, Vincent Setola, Ric Treble, Les Iversen, Kenji Hashimoto: The Ketamine Analogue Methoxetamine and 3- and 4-Methoxy Analogues of Phencyclidine Are High Affinity and Selective Ligands for the Glutamate NMDA Receptor. In: PLoS ONE . 8, 2013, p. E59334, doi : 10.1371 / journal.pone.0059334 .

[pmid6214413-5] Vignon J, Vincent JP, Bidard JN, Kamenka JM, Geneste P, Monier S, Lazdunski M: Biochemical properties of the brain phencyclidine receptor . In: European Journal of Pharmacology . 81, No. 4, July 1982, pp. 531-42. doi : 10.1016 / 0014-2999 (82) 90342-9 . PMID 6214413 .

[pmid2849051-6] Manallack DT, Wong MG, Costa M, Andrews PR, Beart PM: Receptor site topographies for phencyclidine-like and sigma drugs: predictions from quantitative conformational, electrostatic potential, and radioreceptor analyzes . In: Molecular Pharmacology . 34, No. 6, December 1988, pp. 863-79. PMID 2849051 .

[pmid2544905-7] Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R: Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs . In: Pharmacology, Biochemistry and Behavior . 32, No. 3, March 1989, pp. 699-705. doi : 10.1016 / 0091-3057 (89) 90020-8 . PMID 2544905 .

[pmid8267664-8] Manallack DT, Davies JW, Beart PM, Saunders MR, Livingstone DJ: Analysis of the biological and molecular properties of phencyclidine-like compounds by chemometrics . In: drug research . 43, No. 10, October 1993, pp. 1029-32. PMID 8267664 .

[9] Synthesis of 4-Methoxy-PCP

[10] The detection of PCC contamination in PCP and TCP

[11] Illicit Synthesis of Phencyclidine (PCP) and Several of Its Analogs

[12] Andreas Kelich: Encyclopedia of Drugs - PCC

[13] 44th meeting of the Committee of Experts in accordance with Section 1 (2) of the Narcotics Act (BtMG) on May 4th, 2015 at 1 p.m. at the Federal Institute for Drugs and Medical Devices (BfArM, Bonn) . Federal Institute for Drugs and Medical Devices (BfArM). April 4, 2015. Archived from the original on August 28, 2017. Retrieved July 1, 2015.